WO2018143959A1 - Latex polymer - Google Patents
Latex polymer Download PDFInfo
- Publication number
- WO2018143959A1 WO2018143959A1 PCT/US2017/015902 US2017015902W WO2018143959A1 WO 2018143959 A1 WO2018143959 A1 WO 2018143959A1 US 2017015902 W US2017015902 W US 2017015902W WO 2018143959 A1 WO2018143959 A1 WO 2018143959A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- monomer
- latex polymer
- aromatic
- cycloaliphatic
- examples
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/0023—Digital printing methods characterised by the inks used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/0011—Pre-treatment or treatment during printing of the recording material, e.g. heating, irradiating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Definitions
- Latex Polymer Background Inkjet printing with aqueous inks is increasingly being used to print on non- porous flexible and rigid media for signage and other printing applications. It is recognized that inkjet printing of aqueous inks on nonporous media is substantially different than inkjet applications for traditional porous paper-based media. On porous papers, ink drying occurs primarily by ink penetration into the media pore structure, and control of image quality aspects is a strong function of the rate of ink penetration into the media. Thus, optimization of the penetration rate is used for attributes such as optical density and color-to-color bleed. On nonporous media, there is no penetration of the ink into the media, i.e.
- FIG. 1 is a schematic diagram of a printing system for use in an example of a method of printing.
- FIG. 1 is a schematic diagram of a printing system for use in an example of a method of printing.
- co-polymer refers to a polymer that is polymerized from at least two monomers.
- a certain monomer may be described herein as constituting a certain weight percentage of a polymer. This indicates that the repeating units formed from the said monomer in the polymer constitute said weight percentage of the polymer.
- a latex i.e. a latex dispersion including latex polymer particles
- the liquid becomes part of the liquid vehicle of the ink, and thus, latex polymer can be described based on the latex particle or latex polymer solids that remain dispersed in the liquid vehicle.
- the term "monomer emulsion" refers to an organic monomer or monomer mix that is emulsified in an aqueous or water phase. Once the organic monomer or monomer mix is polymerized, a latex polymer dispersion is formed.
- latex polymer dispersion or “latex dispersion” includes both latex particulates as well as the aqueous medium in which the latex particulates are dispersed. More specifically, a latex dispersion is a liquid suspension comprising a liquid (such as water and/or other liquids) and polymeric particulates from 20 nm to 500 nm (preferably from 100 nm to 300 nm) in size (average particle size), and having a weight average molecular weight from about 10,000 Mw to 2,000,000 Mw (preferably from about 100,000 Mw to 300,000 Mw). Such polymeric particulates can comprise a plurality of monomers that are typically randomly polymerized, and can also be crosslinked.
- a liquid such as water and/or other liquids
- polymeric particulates from 20 nm to 500 nm (preferably from 100 nm to 300 nm) in size (average particle size), and having a weight average molecular weight from about 10,000 Mw to 2,000,000 Mw (preferably from about 100,000 Mw to
- the average particle size (e.g. volume or intensity weighted average particle size) may be determined by dynamic light scattering.
- the term“non-porous media” refers to print media which has a Bristow Test of less than 2 ml/m 2 at a contact time of less than 0.5 s.
- test specimen of defined dimensions is affixed to the smooth rim of a wheel free to rotate at a defined constant speed in contact with a stationary test fluid applicator pressing against the test specimen with a defined pressure.
- the test fluid applicator consists of a test solution storage compartment affixed above a 1 by 15-mm test fluid delivery slot, the slot being positioned so that the long dimension is perpendicular to the direction of rotation of the rim of the wheel, and parallel to the wheel axis.
- a defined quantity of test fluid is placed through the fluid reservoir, onto the fluid delivery slot.
- test solution applicator With the wheel with the test specimen affixed rotating at constant speed, the test solution applicator is brought into contact with the rotating test specimen and held in place under defined pressure.
- the test fluid is transferred from the test solution applicator onto the test specimen in a band whose width, controlled by the applicator slot width is approximately 15 mm, and whose length is function of the absorptive characteristics of the test fluid interaction with the test specimen under the defined test conditions.
- the amount of liquid absorbed per unit area of test specimen is calculated from the volume of test fluid originally placed in the applicator, and the average width and length of the band created on the test specimen by the transferred test fluid.
- the time available for the liquid absorption is calculated from the volume of test fluid originally placed in the applicator and applicator geometry.
- ink vehicle refers to the liquid fluid in which a latex polymer and a pigment are placed to form an ink.
- Ink vehicles may include a mixture of a variety of different agents, including, for example, surfactants, solvents, co-solvents, buffers, biocides, viscosity modifiers, sequestering agents, stabilizing agents, humectants and water.
- decap is a measure of how long a printing nozzle may remain inactive before plugging and how many inkjet architecture firings are required to re- establish proper drop ejection.
- the term“(meth)acrylate” is well understood in the art to refer to both acrylates and methacrylates.
- cyclohexyl (meth)acrylate refers to cyclohexyl acrylate and/or cyclohexyl methacrylate.
- cycloaliphatic (meth)acrylate monomer denotes a cycloaliphatic acrylate monomer and/or a cycloaliphatic methacrylate monomer; and the term“aromatic(meth)acrylate monomer” denotes an aromatic acrylate monomer and/or an aromatic methacrylate monomer.
- aromatic(meth)acrylate monomer denotes an aromatic acrylate monomer and/or an aromatic methacrylate monomer.
- (meth)acrylamide is well understood in the art to refer to both acrylamides and methacrylamides.
- cycloaliphatic (meth)acrylamide monomer denotes a cycloaliphatic acrylamide monomer and/or a cycloaliphatic methacrylamide monomer
- aromatic (meth)acrylamide monomer denotes an aromatic acrylamide monomer and/or an aromatic methacrylamide monomer
- a numerical range of "about 1 wt% to about 5 wt%" should be interpreted to include not just the explicitly recited values of about 1 wt% to about 5 wt%, but also include individual values and subranges within the indicated range. Thus, included in this numerical range are individual values such as 2, 3.5, and 4 and sub-ranges such as from 1-3, from 2-4, and from 3-5, etc. This same principle applies to ranges reciting a single numerical value. Furthermore, such an interpretation should apply regardless of the breadth of the range or the characteristics being described. [00020] Unless otherwise stated, any feature described herein can be combined with any aspect or any other feature described herein.
- non-porous media for outdoor signage are typically PVC-based, which is relatively easy to adhere to with conventional latex inkjet inks
- other non-porous media e.g. rigid media
- Adhesion to low energy surfaces e.g., polyethylene, polypropylene
- This problem has been encountered in many industries as the need to use inexpensive recyclable parts has increased.
- Previous solutions to inkjet printing on a wide variety of non-porous substrates have employed primers which are applied to the non-porous media before printing.
- the present inventors have found that in order to print on a wide range of non- porous media in-printer ink drying and curing of inkjet compositions should take place at a media temperature of about 70 oC or less, for example about 65 oC or less to avoid media deformation which may occur at higher temperatures. Therefore, the present inventors have sought to provide latex polymers and inkjet ink compositions comprising such latex polymers which adhere to a wide range of substrates, particularly non-porous substrates, e.g. rigid and non-porous substrates, without the need for primer coating prior to printing of the inject inks and which also provide good decap performance and provide excellent pigment binding resulting in excellent pigment retention upon environmental exposure.
- latex polymer derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- an inkjet ink composition comprising a latex polymer and an ink vehicle, wherein the latex polymer is derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- a method of inkjet printing comprising: providing a non-porous print substrate; and inkjet printing an inkjet ink composition to the print substrate to form an ink layer on the print substrate, wherein the inkjet ink composition comprises a latex polymer and an ink vehicle, wherein the latex polymer is derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- Latex polymer Described herein is a latex polymer derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- the latex polymer may comprise a copolymer of a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises one or more monomers comprising a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer, and the aromatic monomer comprises one or more monomers comprising an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- the latex polymer may comprise a copolymer comprising cycloaliphatic monomer units (e.g. cycloaliphatic (meth)acrylate and/or cycloaliphatic (meth)acrylamide units) and aromatic monomer units (e.g.
- the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer.
- the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer.
- a cycloaliphatic (meth)acrylate monomer is a monomer comprising a cycloaliphatic moiety bonded to, either directly or indirectly, a (meth)acrylate moiety (e.g.
- the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylamide monomer.
- a cycloaliphatic (meth)acrylamide monomer is a monomer comprising a cycloaliphatic moiety bonded to, either directly or indirectly, a (meth)acrylamide moiety (e.g.
- the cycloaliphatic moiety comprises a 5-12 membered aliphatic ring, for example a carbon ring having 5-12 carbon atoms (e.g. a C 5 -C 12 ring), or a 5-12 membered heteroaliphatic ring.
- the cycloaliphatic moiety comprises a C 5 -C 12 ring, a C 5 -C 12 ring may be a single ring (such as cyclopentyl, cyclohexyl or cycloheptyl groups) or a bicyclic ring (such as decalin).
- the cycloaliphatic moiety comprises a 5-10 membered aliphatic ring, for example a 6-10 membered aliphatic ring.
- the cycloaliphatic moiety comprises a carbon ring having 5- 10 carbon atoms (e.g. a C 5 -C 10 ring).
- the cycloaliphatic moiety comprises a carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 ring).
- the cycloaliphatic moiety comprises a substituent, such as an alkyl, heteroalkyl, alkoxy, hydroxyl, cycloaliphatic or aromatic substituent.
- the cycloaliphatic moiety comprises a substituent, such as an alkyl group (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group), an aryl group (e.g.
- the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer. In some examples, the aromatic monomer comprises an aromatic (meth)acrylate monomer.
- An aromatic (meth)acrylate monomer is a monomer comprising an aromatic moiety bonded to, either directly or indirectly, a (meth)acrylate moiety (e.g. by a carbon chain, for example a substituted or unsubstituted carbon chain, for example a saturated or unsaturated carbon chain, such as a C 1-12 carbon chain, for example a C 1-10 carbon chain, a C 1-6 carbon chain, or a C 1-4 carbon chain, wherein one or more of the carbon atoms may be replaced by a heteroatom such as oxygen, nitrogen or sulfur, for example oxygen).
- the aromatic monomer comprises an aromatic (meth)acrylamide monomer.
- An aromatic (meth)acrylamide monomer is a monomer comprising an aromatic moiety bonded to, either directly or indirectly, a (meth)acrylamide moiety (e.g. by a carbon chain; for example a substituted or unsubstituted carbon chain, for example a saturated or unsaturated carbon chain, such as a C 1-12 carbon chain, for example a C 1-10 carbon chain, a C 1-6 carbon chain, or a C 1-4 carbon chain, wherein one or more of the carbon atoms may be replaced by a heteroatom such as oxygen, nitrogen or sulfur, for example oxygen).
- the aromatic moiety comprises a 5-12 membered aromatic ring, for example an aromatic carbon ring having 6-12 carbon atoms (e.g.
- the aromatic moiety comprises a C5-C12 aromatic ring, a C5-C12 aromatic ring may be a single aromatic ring (e.g. benzyl or phenyl), or a bicyclic aromatic ring (e.g. naphthyl).
- the aromatic moiety comprises a 5-10 membered aromatic ring, for example a 6-10 membered aromatic ring.
- the aromatic moiety comprises an aromatic carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 aromatic ring).
- the aromatic moiety comprises a substituent, such as an alkyl, heteroalkyl (including an ether containing group), alkoxy, hydroxyl, cycloaliphatic or aromatic substituent.
- the aromatic moiety comprises a substituent.
- the aromatic moiety may be substituted by an alkyl group, (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group), an aryl group (e.g. a C 5-12 aryl group, for example C 5-10 aryl group), a heteroalkyl group (e.g.
- the cycloaliphatic monomer is a cycloaliphatic monomer having the formula (I) formula (I) wherein,
- R 1 is H or methyl
- Z is O or NR 2 , where R 2 is H, alkyl or X’;
- Y is a bond or a carbon chain, where one or more of the carbon atoms of the carbon chain may be replaced with a heteroatom such as oxygen, sulfur or nitrogen;
- X and X’ are independently cycloaliphatic moieties.
- R 2 is alkyl, for example C 1-12 , C 1-10 , C 1-6 , or C 1-4 alkyl (e.g. methyl or ethyl).
- R 2 is an optionally substituted alkyl group.
- R2 is H, an optionally substituted alkyl group or X’.
- R2 is H or X’.
- R 2 is H.
- Y is a bond or a saturated or unsaturated carbon chain.
- Y is a bond or a C 1-12 , for example C 1-10 , C 1-6 , or C 1-4 carbon chain.
- one or more of the carbon atoms of the carbon chain represented by Y is replaced with a heteroatom selected from oxygen, sulfur and nitrogen.
- Y is a bond.
- X is a 5-12 membered ring, for example a carbon ring having 5-12 carbon atoms (e.g. a C 5 -C 12 ring), or a 5-12 membered heteroaliphatic ring.
- X is a C 5 -C 12 single ring (such as cyclopentyl, cyclohexyl or cycloheptyl groups) or a bicyclic ring (such as decalin).
- X is a carbon ring having 5-10 carbon atoms (e.g. a C 5 -C 10 ring). In some examples, X is a carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 ring). [00043] In some examples, X is substituted, for example with an alkyl, alkoxy, hydroxyl, heteroalkyl, cycloaliphatic or aromatic substituent. In some examples, X is substituted with an alkyl group (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group),an aryl group (e.g.
- a C 5-12 aryl group for example C5-10 aryl group
- a heteroalkyl group e.g. a C1-12 heteroalkyl (such as ether containing group), for example C 1-10 heteroalkyl, C 1-6 heteroalkyl, C 1-4 heteroalkyl (e.g. C 1-4 ether)
- X is optionally substituted, for example optionally substituted with a C 1-12 alkyl group.
- X’ is a carbon ring having 5-12 carbon atoms (e.g. a C5-C12 ring), or a 5-12 membered heteroaliphatic ring.
- X’ is a C 5 -C 12 single ring (such as cyclopentyl, cyclohexyl or cycloheptyl groups) or a bicyclic ring (e.g a C6 or C10 fused ring, such as decalin).
- X’ is a carbon ring having 5-10 carbon atoms (e.g. a C 5 -C 10 ring).
- X’ is a carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 ring).
- X’ is substituted, for example with an alkyl, alkoxy, hydroxyl, heteroalkyl, cycloaliphatic or aromatic substituent.
- X’ is substituted with an alkyl group (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group),an aryl group (e.g. a C 5-12 aryl group, for example C 5-10 aryl group), a heteroalkyl group (e.g.
- a C 1-12 heteroalkyl such as ether containing group
- C 1-10 heteroalkyl for example C 1-10 heteroalkyl, C 1-6 heteroalkyl, C 1-4 heteroalkyl (e.g. C 1-4 ether)
- X’ is optionally substituted, for example optionally substituted with a C 1-12 alkyl group.
- Z is NR 2 and R 2 is X’
- X and X’ may be the same.
- cycloaliphatic monomers include: cyclohexyl acrylate, cyclohexyl methacrylate, methylcyclohexyl acrylate, methylcyclohexyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, and other cycloaliphatic methacrylate and acrylate monomers including ester derivatives of decalinol, hydrogenated bisphenol A and F.
- the latex polymer comprises at least about 50 wt% cycloaliphatic monomers by total weight solids of the latex polymer, for example at least about 55 wt%, or at least about 60 wt% cycloaliphatic monomers by total weight solids of the latex polymer. [00049] In some examples, the latex polymer comprises up to about 95 wt% cycloaliphatic monomers by total weight solids of the latex polymer, for example up to about 90 wt% cycloaliphatic monomers by total weight solids of the latex polymer.
- the latex polymer comprises from about 50 wt% to about 90 wt%, for example from about 60 wt% to about 90 wt% cycloaliphatic monomers by total weight solids of the latex polymer.
- the aromatic monomer is an aromatic monomer having the formula (II)
- R 1 is H or methyl
- Z is O or NR 2 , where R 2 is H, alkyl or W’;
- Y is a bond or a carbon chain, where one or more of the carbon atoms of the carbon chain may be replaced with a heteroatom such as oxygen, sulfur or nitrogen;
- W and W’ are independently aromatic moieties.
- R 2 is alkyl, for example C 1-12 , C 1-10 , C 1-6 , or C 1-4 alkyl (e.g. methyl or ethyl).
- R 2 is an optionally substituted alkyl group.
- R 2 is H, an optionally substituted alkyl group or W’.
- R 2 is H or W’.
- R 2 is H.
- Y is a bond or a saturated or unsaturated carbon chain.
- Y is a bond or a C 1-12 , for example C 1-10 , C 1-6 , or C 1-4 carbon chain.
- W is a 5-12 membered aromatic ring, for example a carbon ring having 6-12 carbon atoms (e.g. a C 6 -C 12 aromatic ring), or a 5-12 membered heteroaromatic ring.
- W comprises a C 5 -C 12 aromatic ring, a C 5 -C 12 aromatic ring may be a single aromatic ring (e.g.
- W is a 5-10 membered aromatic ring, for example a 6-10 membered aromatic ring.
- W is an aromatic carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 aromatic ring).
- W is substituted, for example W may be substituted with an alkyl group (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group),an aryl group (e.g. a C 5-12 aryl group, for example C 5-10 aryl group), a heteroalkyl group (e.g. a C 1-12 heteroalkyl (such as ether containing group), for example C1-10 heteroalkyl, C1-6 heteroalkyl, C1-4 ether).
- W is optionally substituted, for example optionally substituted with a C 1-12 alkyl group.
- W’ is a 5-12 membered aromatic ring, for example a carbon ring having 6-12 carbon atoms (e.g. a C6-C12 aromatic ring), or a 5-12 membered heteroaromatic ring.
- W’ comprises a C 6 -C 12 aromatic ring, a C 6 -C 12 aromatic ring may be a single aromatic ring (e.g. benzyl or phenyl) or a bicyclic aromatic ring (e.g. a fused C6 or C10 aromatic ring, e.g. naphthyl).
- W’ is a 5-10 membered aromatic ring, for example a 6-10 membered aromatic ring.
- W’ is an aromatic carbon ring having 6-10 carbon atoms (e.g. a C 6 -C 10 aromatic ring).
- W’ is substituted, for example, W’ may be substituted with an alkyl group (for example a C 1-12 alkyl group, for example C 1-10 alkyl group, C 1-6 alkyl group, C 1-4 alkyl group, or a methyl group),an aryl group (e.g. a C 5-12 aryl group, for example C 5-10 aryl group), a heteroalkyl group (e.g.
- W is optionally substituted, for example optionally substituted with a C 1-12 alkyl group.
- W and W may be the same.
- aromatic monomers include: 2-phenoxyethyl methacrylate, 2- phenoxyethyl acrylate, phenyl propyl methacrylate, phenyl propyl acrylate, benzyl methacrylate, benzyl acrylate, phenylethyl methacrylate, phenylethyl acrylate, benzhydryl methacrylate, benzhydryl acrylate, N-benzyl methacrylate, N-benzyl acrylate, N,N-diphenyl methacrylamide, N,N-diphenyl acrylamide, naphthyl methacrylate, naphthyl acrylate, phenyl methacrylate and phenyl acrylate.
- the latex polymer comprises at least about 1 wt% aromatic monomers by total weight solids of the latex polymer, for example at least about 2 wt%, or at least about 5 wt% aromatic monomers by total weight solids of the latex polymer.
- the latex polymer comprises up to about 35 wt% aromatic monomers by total weight solids of the latex polymer, for example up to about 30 wt%, up to about 25 wt%, or up to about 20 wt% aromatic monomers by total weight solids of the latex polymer.
- the latex polymer comprises from about 1 wt% to about 35 wt% aromatic monomers by total weight solids of the latex polymer, for example from about 2 wt% to about 30 wt%, or about 5 wt% to about 25 wt% aromatic monomers by total weight solids of the latex polymer.
- the latex polymer has a glass transition temperature of about 20 oC or greater, for example about 30 oC or greater, about 40 oC or greater, about 45 oC or greater, or about 50 oC or greater.
- the latex polymer has a glass transition temperature of up to about 100 oC, for example up to about 95 oC, up to about 90 oC, up to about 80 oC, or up to about 70 oC.
- the latex polymer has a glass transition temperature in the range of about 20 oC to about 100 oC, for example about 30 oC to about 90 oC, about 50 oC to about 90 oC, or about 55 oC to about 70 oC.
- the glass transition temperature (Tg) of the latex polymer may be estimated using the Fox equation (T. G. Fox, Bull. Am.
- the maximum Tg of each of the homopolymers of each of the monomers making up to copolymer of the latex polymer may be taken from literature values (for example as listed in“Polymer Handbook”, edited by J. Brandrup, E.H. Immergut, and E.A. Grulke, Wiley Publishers, 4 th edition).
- the glass transition temperature of the latex polymer may also be determined using DSC (differential scanning calorimetry) according to ASTM D3418.
- the composition from which the latex polymer is derived further comprises an alkyl meth(acrylate). In some examples, the composition from which the latex polymer is derived comprises an alkyl methacrylate monomer. In some examples, the composition from which the latex polymer is derived comprises an alkyl acrylate monomer. In some examples, the composition from which the latex polymer is derived comprises an alkyl acrylate monomer and an alkyl methacrylate monomer. In some examples, the alkyl (meth)acrylate may be a C 1-8 alkyl (meth)acrylate. [00070] In some examples, the latex polymer comprises an alkyl meth(acrylate) component.
- the latex polymer further comprises an alkyl methacrylate component. In some examples, the latex polymer further comprises an alkyl acrylate component. In some examples, the latex polymer further comprises an alkyl acrylate component and an alkyl methacrylate component. [00071] In some examples, the latex polymer comprises from about 0 wt% to about 10 wt%, for example from about 0.1 wt% to about 10 wt% of an alkyl meth(acrylate), for example methyl methacrylate. [00072] In some examples, the latex polymer comprises a copolymer formed from an alkyl meth(acrylate) monomer, a cycloaliphatic monomer and an aromatic monomer.
- the latex polymer comprises a copolymer formed from an alkyl meth(acrylate) monomer, (meth)acrylic acid, a cycloaliphatic monomer and an aromatic monomer. In some examples, the latex polymer comprises a copolymer formed from a (meth)acrylic acid, a cycloaliphatic monomer and an aromatic monomer. [00073] In some examples, the composition from which the latex polymer is derived further comprises an acid monomer, for example (meth)acrylic acid monomers or carboxylic acid monomers. In some examples, the composition from which the latex polymer is derived further comprises (meth)acrylic acid.
- the composition may comprise (meth)acrylic acid in an amount of 0 wt% to about 15 wt%, about 0.1 wt% to about 15 wt%, for example, about 0.25 wt% to about 10 wt%, or about 0.25 wt% to about 6 wt%.
- the composition from which the latex polymer is derived further comprises methacrylic acid.
- the composition may comprise methacrylic acid in an amount of 0 wt% to about 15 wt%, about 0.1 wt% to about 15 wt%, for example, about 0.25 wt% to about 10 wt%, or about 0.25 wt% to about 6 wt%.
- the composition from which the latex polymer is derived further comprises an alkyl meth(acrylate) monomer and/or (meth)acrylic acid. In some examples, the composition from which the latex polymer is derived further comprises an alkyl meth(acrylate) monomer and (meth)acrylic acid. [00075] In some examples, the latex polymer substantially lacks a styrene component.
- the latex polymer may comprise less than about 5 wt% styrene by total weight solids of the latex polymer, for example less than about 4 wt%, less than about 3 wt%, less than about 2 wt%, less than about 1 wt%, less than about 0.5 wt%, or less than about 0.1 wt% styrene by total weight solids of the latex polymer.
- the latex polymer lacks a styrene component.
- the latex polymer may be prepared by copolymerizing the monomer components with a copolymerizable surfactant (for example surfactants from the Hitenol ® AR series or Hitenol ® BC series, e.g. Hitenol ® BC-10, BC-30, KH-05 or KH-10) to form a latex dispersion.
- a copolymerizable surfactant for example surfactants from the Hitenol ® AR series or Hitenol ® BC series, e.g. Hitenol ® BC-10, BC-30, KH-05 or KH-10) to form a latex dispersion.
- the latex polymer is prepared by combining the monomers as an aqueous emulsion with an initiator.
- an initiator may be used.
- the initiator may be selected from a persulfate, such as a metal persulfate or an ammonium persulfate.
- a latex dispersion comprises latex polymer particles dispersed in water.
- Inkjet Ink Composition Described herein is an inkjet ink composition comprising a latex polymer and an ink vehicle, wherein the latex polymer is derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- the latex ink composition comprise a latex polymer, a pigment and an ink vehicle.
- the latex polymer of the inkjet ink composition may be as described above.
- the inkjet ink composition comprises up to about 35 wt% pigment and latex polymer solids by total weight of the composition, for example up to about 30 wt%, about 25 wt% or up to about 20 wt% pigment and latex polymer solids by total weight of the composition.
- the inkjet ink composition comprises from about 0.5 wt% to about 35 wt% pigment and latex polymer solids by total weight of the composition, for example from about 1 wt% to about 30 wt%, from about 1 wt% to about 25 wt%, or from about 2 wt% to about 20 wt% pigment and latex polymer solids by total weight of the composition.
- the present inventors have found that compositions having a total amount of pigment and latex polymer solids within these ranges may be suitable for inkjet printing, for example for thermal inkjet printing.
- the inkjet ink composition comprises at least about 3 wt% latex polymer by total weight of the composition, for example at least about 5 wt% latex polymer by total weight of the composition. In some examples, the inkjet ink composition comprises up to about 25 wt% latex polymer by total weight of the composition, for example up to about 20 wt%, or up to about 15 wt% latex polymer by total weight of the composition. In some examples, the inkjet ink composition comprises from about 3 wt% to about 25 wt%, for example about 5 wt% to about 25 wt% latex polymer by total weight of the composition.
- the inkjet ink composition comprises at least about 0.1 wt% pigment by total weight of the composition, for example, at least about 0.3 wt% pigment by total weight of the composition. In some examples, the inkjet ink composition comprises up to about 30 wt% pigment by total weight of the composition, for example, up to about 20 wt% pigment by total weight of the composition, or up to about 15 wt% pigment by total weight of the composition. In some examples, the inkjet ink composition comprises from about 0.1 wt% to about 30 wt%, for example 0.3 wt% to about 30 wt% pigment by total weight of the composition.
- the inkjet ink composition comprises an amount of pigment and an amount of latex polymer, such that the ratio of the amount of pigment to amount of latex by weight is in the range of about 0.1:15 to 10:5.
- the inkjet ink composition substantially lacks a styrene component.
- the inkjet ink composition may comprise less than about 5 wt% styrene by total weight solids of the latex polymer, for example less than about 4 wt%, less than about 3 wt%, less than about 2 wt%, less than about 1 wt%, less than about 0.5 wt%, or less than about 0.1 wt% styrene by total weight solids of the latex polymer.
- Pigment [00087]
- the inkjet ink composition comprises a pigment.
- the inkjet ink composition may comprise a latex polymer, a pigment, and an ink vehicle.
- the inkjet ink composition is unpigmented or substantially lacks a pigment.
- the inkjet ink composition may comprise less than 0.5 wt% of a pigment, for example less than 0.1 wt% of a pigment or less than 0.05 wt% of a pigment by total weight of the composition.
- the inkjet ink composition is unpigmented and lacks a pigment, for example the inkjet ink composition may be a colourless composition.
- the term "pigment" can include particulate dispersible colorants that can be suspended or dispersed in a liquid vehicle in accordance with embodiments of the present invention.
- the pigment itself can be a self-dispersed pigment or a non-self-dispersed pigment.
- the pigment may include black pigments, white pigments, cyan pigments, magenta pigments, yellow pigments, or the like.
- Suitable inorganic pigments include, for example, carbon black.
- other inorganic pigments may be suitable such as titanium oxide, cobalt blue (CoO-Al 2 O 3 ), chrome yellow (PbCrO 4 ), and iron oxide.
- Suitable organic pigments include, for example, azo pigments including diazo pigments and monoazo pigments, polycyclic pigments (e.g., phthalocyanine pigments such as phthalocyanine blues and phthalocyanine greens, perylene pigments, perinone pigments, anthraquinone pigments, quinacridone pigments, dioxazine pigments, thioindigo pigments, isoindolinone pigments, pyranthrone pigments, and quinophthalone pigments), insoluble dye chelates (e.g., basic dye type chelates and acidic dye type chelate), nitropigments, nitroso pigments, and the like.
- phthalocyanine pigments such as phthalocyanine blues and phthalocyanine greens
- perylene pigments perinone pigments
- anthraquinone pigments quinacridone pigments
- dioxazine pigments thioindigo pigments
- phthalocyanine blues include copper phthalocyanine blue and derivatives thereof (Pigment Blue 15).
- quinacridones include Pigment Orange 48, Pigment Orange 49, Pigment Red 122, Pigment Red 192, Pigment Red 202, Pigment Red 206, Pigment Red 207, Pigment Red 209, Pigment Violet 19 and Pigment Violet 42.
- anthraquinones include Pigment Red 43, Pigment Red 194 (Perinone Red), Pigment Red 216 (Brominated Pyranthrone Red) and Pigment Red 226 (Pyranthrone Red).
- perylenes include Pigment Red 123 (Vermillion), Pigment Red 149 (Scarlet), Pigment Red 179 (Maroon), Pigment Red 190 (Red), Pigment Violet 19, Pigment Red 189 (Yellow Shade Red) and Pigment Red 224.
- thioindigoids include Pigment Red 86, Pigment Red 87, Pigment Red 88, Pigment Red 181, Pigment Red 198, Pigment Violet 36, and Pigment Violet 38.
- heterocyclic yellows include Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 17, Pigment Yellow 65, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 151, Pigment Yellow 117, Pigment Yellow 128 and Pigment Yellow 138, Pigment Yellow 155, Pigment Yellow 83, and Pigment Yellow 213.
- Such pigments are commercially available in either powder or press cake form from a number of sources including, BASFTM Corporation, EngelhardTM Corporation and Sun ChemicalTM Corporation.
- black pigments that can be used include carbon pigments.
- the carbon pigment can be almost any commercially available carbon pigment that provides acceptable optical density and print characteristics.
- Carbon pigments suitable for use in the present system and method include, without limitation, carbon black, graphite, vitreous carbon, charcoal, and combinations thereof.
- Such carbon pigments can be manufactured by a variety of known methods such as a channel method, a contact method, a furnace method, an acetylene method, or a thermal method, and are commercially available from such vendors as CabotTM Corporation, Columbian Chemicals Company, Degussa AGTM, and E.I. DuPontTM de Nemours and Company.
- Suitable carbon black pigments include, without limitation, Cabot pigments such as MONARCHTM 1400, MONARCHTM 1300, MONARCHTM 1100, MONARCHTM 1000, MONARCHTM 900, MONARCHTM 880, MONARCHTM 800, MONARCHTM 700, CAB-O-JETTM 200, CAB-O-JETTM 300, REGALTM, BLACK PEARLS, ELFTEXTM, MOGULTM, and VULCANTM pigments; Columbian pigments such as RAVENTM 7000, RAVENTM 5750, RAVENTM 5250, RAVENTM 5000, and RAVENTM 3500; Degussa pigments such as Color Black FW 200, RAVENTM FW 2, RAVENTM FW 2V, RAVENTM FW 1, RAVENTM FW 18, RAVENTM S160, RAVENTM FW S170, Special BlackTM 6, Special BlackTM 5, Special BlackTM 4A, Special BlackTM 4, PRINTEXTM U
- colored pigments can be used with the inkjet ink composition, therefore the following listing is not intended to be limiting.
- colored pigments can be blue, brown, cyan, green, white, violet, magenta, red, orange, yellow, as well as mixtures thereof.
- the following color dispersions are available from CabotTM Corp. CABO-JETTM 250C, CABO-JETTM 260M, and CABO-JETTM 270Y.
- PALIOGENTM Orange PALIOGENTM Orange 3040, PALIOGENTM Blue L 6470, PALIOGENTM Violet 5100, PALIOGENTM Violet 5890, PALIOGENTM Yellow 1520, PALIOGENTM Yellow 1560, PALIOGENTM Red 3871K, PALIOGENTM Red 3340, HELIOGENTM Blue L 6901F, HELIOGENTM Blue NBD 7010, HELIOGENTM Blue K 7090, HELIOGENTM Blue L 7101F, HELIOGENTM Blue L6900, L7020, HELIOGENTM Blue D6840, HELIOGENTM Blue D7080, HELIOGENTM Green L8730, HELIOGENTM Green K 8683, and HELIOGENTM Green L 9140.
- the following pigments are available from Ciba-Geigy Corp.: CHROMOPHTALTM Yellow 3G, CHROMOPHTALTM Yellow GR, CHROMOPHTALTM Yellow 8G, IGRAZINTM Yellow 5GT, IGRALITETM Rubine 4BL, IGRALITETM Blue BCA, MONASTRALTM Magenta, MONASTRALTM Scarlet, MONASTRALTM Violet R, MONASTRALTM Red B, and MONASTRALTM Violet Maroon B.
- the following pigments are available from Heubach GroupTM: DALAMARTM Yellow YT-858-D and HEUCOPHTHALTM Blue G XBT-583D.
- the following pigments are available from Hoechst Specialty ChemicalsTM: Permanent Yellow GR, Permanent Yellow G, Permanent Yellow DHG, Permanent Yellow NCG-71, Permanent Yellow GG, Hansa Yellow RA, Hansa Brilliant Yellow 5GX-O2, Hansa Yellow- X, NOVOPERMTM Yellow HR, NOVOPERMTM Yellow FGL, Hansa Brilliant Yellow 10GX, Permanent Yellow G3R-01, HOSTAPERMTM Yellow H4G, HOSTAPERMTM Yellow H3G, HOSTAPERMTM Orange GR, HOSTAPERMTM Scarlet GO, HOSTAPERMTM Pink E, Permanent Rubine F6B, and the HOSTAFINETM series.
- the following pigments are available from Mobay Corp.: QUINDOTM Magenta, INDOFASTTM Brilliant Scarlet, QUINDOTM Red R6700, QUINDOTM Red R6713, and INDOFASTTM Violet.
- the following pigments are available from Sun Chemical Corp.: L74-1357 Yellow, L75-1331 Yellow, and L75-2577 Yellow.
- pigments can include Normandy Magenta RD-2400, Permanent Violet VT2645, Argyle Green XP-111-S, Brilliant Green Toner GR 0991, Sudan Blue OS, PV Fast Blue B2GO1, Sudan III, Sudan II, Sudan IV, Sudan Orange G, Sudan Orange 220, Ortho Orange OR 2673, Lithol Fast Yellow 0991 K, Paliotol Yellow 1840, Lumogen Yellow D0790, Suco-Gelb L1250, Suco-Yellow D1355, Fanal Pink D4830, Cinquasia Magenta, Lithol Scarlet D3700, Toluidine Red, Scarlet for Thermoplast NSD PS PA, E. D.
- Toluidine Red Toluidine Red
- Lithol Rubine Toner Lithol Scarlet 4440
- Bon Red C Royal Brilliant Red RD-8192
- Oracet Pink RF Lithol Fast Scarlet L4300
- white TIPURE R- 101 These pigments are available from commercial sources such as Hoechst Celanese CorporationTM, Paul Uhlich, BASF, American HoechstTM, Ciba-GeigyTM, AldrichTM, DuPontTM, Ugine Kuhlman of CanadaTM, Dominion Color CompanyTM, MagruderTM, and MathesonTM. Examples of other suitable colored pigments are described in the Colour Index, 3rd edition (The Society of Dyers and Colourists, 1982).
- the ink vehicle of the inkjet ink composition comprises water.
- the water, or a portion of the water, of the ink vehicle may be introduced to the ink vehicle as a latex polymer emulsion is combined with the first and second solvents of the ink vehicle.
- additional water may be added to the inkjet ink composition.
- the inkjet ink composition comprises water.
- the inkjet ink composition comprises at least about 20 wt%, for example at least about 30 wt%, at least about 40 wt%, or at least about 50 wt% by total weight of the composition.
- the inkjet ink composition comprises up to about 90 wt% water, for example up to about 85 wt%, up to about 80 wt%, or up to about 75 wt% by total weight of the composition.
- the inkjet ink composition comprises water in an amount from about 20 wt% to about 85 wt% by total weight of the inkjet ink composition, for example about 30 wt% to about 80 wt%, about 40 wt% to about 80 wt%, or from about 50% to about 75% water.
- the ink vehicle comprises water and a co-solvent (for example a blend of co-solvents).
- the inkjet ink composition comprises the co-solvent in an amount of at least about 1 wt%, for example at least about 5 wt%, or at least about 10 wt% by total weight of the composition. In some examples, the inkjet ink composition comprises the co-solvent in an amount up to about 50 wt%, for example up to about 40 wt%, or up to about 35 wt% by total weight of the composition. In some examples the inkjet ink composition comprises a co-solvent in an amount of about 1 to about 50 wt% by total weight of the composition, for example from about 5 to about 40 wt% of the composition, or about 10 to about 35 wt% of the total weight of the composition.
- the ink vehicle comprises a co-solvent having a boiling point ranging from 160°C to 285°C. In some examples, the ink vehicle comprises a co-solvent having a boiling point ranging from 170°C to 250°C, for example from 170°C to 220°C, or 170°C to 215°C. In some examples, the ink vehicle comprises a co-solvent having a boiling point of about 215°C or less.
- the co-solvent may be selected form organic co-solvents including aliphatic alcohols, aromatic alcohols, diols, glycol ethers, polyglycol ethers, caprolactams, formamides, acetamides, and long chain alcohols.
- the co-solvent may be selected form primary aliphatic alcohols, secondary aliphatic alcohols, 1,2-alcohols, 1,3-alcohols, 1,4-alcohols, 1,5-alcohols, ethylene glycol alkyl ethers, propylene glycol alkyl ethers, higher homologs (C6-C12) of polyethylene glycol alkyl ethers, pyrrolidinones, N-alkyl caprolactams, unsubstituted caprolactams, both substituted and unsubstituted formamides, both substituted and unsubstituted acetamides, and combinations thereof.
- the co-solvent comprises a first solvent having a boiling point of about 215 oC or less and a second solvent having a boiling point of at least about 220 oC.
- the ink vehicle of the inkjet ink composition comprises a first solvent having a boiling point of about 212 oC or less, for example about 210 oC or less, for example about 205 oC or less.
- the first solvent has a boiling point of at least about 170 oC, for example at least about 175 oC, at least about 180 oC, or at least about 185 oC.
- the first solvent has a boiling point in the range of about 170 oC to about 215 oC. In some examples, the first solvent has a boiling point in the range of about 180 oC to about 215 oC, for example about 185 oC to about 215 oC, or about 185 oC to about 210 oC. [000100] In some examples, the first solvent is selected from an aliphatic alcohol, for example a primary aliphatic alcohol, a secondary aliphatic alcohol or a tertiary aliphatic alcohol. The aliphatic alcohol may be a diol.
- the first solvent is an aliphatic alcohol containing 10 carbons or less, for example 8 carbons or less or 6 carbons or less. In some examples, the first solvent is an aliphatic alcohol being a diol containing 10 carbons or less, for example 8 carbons or less or 6 carbons or less. [000101] In some examples, the first solvent is selected from the group comprising 1,2-propanediol, 1,2-butanediol, ethylene glycol, 2-methyl-2,4-pentanediol, 1,3-butanediol, 2-methyl-1,3-propanediol and 1,3-propanediol.
- the first solvent is selected from the group comprising 1,2-propanediol, 1,2-butanediol, ethylene glycol, 2- methyl-2,4-pentanediol, and 1,3-butanediol. In some examples the first solvent is selected from the group consisting of 1,2-propanediol, 1,2-butanediol, ethylene glycol, 2-methyl-2,4- pentanediol, 1,3-butanediol, 2-methyl-1,3-propanediol and 1,3-propanediol.
- the first solvent is selected from the group consisting of 1,2-propanediol, 1,2- butanediol, ethylene glycol, 2-methyl-2,4-pentanediol, and 1,3-butanediol. In some examples the first solvent is 1,2-butanediol.
- the inkjet ink composition comprises at least about 1 wt% of the first solvent by total weight of the composition, for example, at least about 5 wt%, at least about 10 wt%, or at least about 15 wt% by total weight of the composition.
- the inkjet ink composition comprises up to about 40 wt% of the first solvent by total weight of the composition, for example up to about 30 wt%, or up to about 20 wt% by total weight of the composition.
- the inkjet ink composition comprises the first solvent in an amount of from about 1 wt% to about 40 wt% by total weight of the composition, for example from about 5 wt% to about 40 wt%, about 10 wt% to about 30 wt%, or from about 15 wt% to about 20 wt% by total weight of the composition.
- the ink vehicle of the inkjet ink composition comprises a second solvent having a boiling point of at least about 220 oC, for example at least about 225 oC.
- the second solvent has a boiling point up to about 285 oC, for example up to about 280 oC.
- the second solvent has a boiling point in the range of about 220 oC to about 285 oC, for example about 225 oC to about 285 oC.
- the second solvent is selected from alcohols (including aliphatic alcohols and aromatic alcohols), esters, glycol ethers, di- and trialkylene glycols, amides, lactams and sulfones.
- the solvent is selected from aliphatic alcohols (including primary, secondary and tertiary aliphatic alcohols, including diols), aromatic alcohols, esters, glycol alkyl ethers (such as alkylene glycol alkyl ethers, including di-, tri- and tetra- alkylene glycol alkyl ethers), glycol aryl ethers (such as alkylene glycol aryl ethers, including di- and tri- alkylene glycol aryl ethers), di- and tri-alkylene glycols, lactams (such as 2-pyrrolidinone) and sulfones (such as sulfolane).
- aliphatic alcohols including primary, secondary and tertiary aliphatic alcohols, including diols
- aromatic alcohols esters
- glycol alkyl ethers such as alkylene glycol alkyl ethers, including di-, tri- and tetra- alkylene glycol alkyl
- the second solvent is selected from aliphatic alcohols containing 20 carbons or less (for example aliphatic alcohols containing 10 carbons or less), esters containing 20 carbons or less (for example esters containing 12 carbons or less), glycol alkyl ethers, such as alkylene glycol alkyl ethers, containing 20 carbons or less (for example esters containing 12 carbons or less, or 10 carbons or less), glycol aryl ethers, such as alkylene glycol aryl ethers, containing 20 carbons or less (for example esters containing 12 carbons or less, or 10 carbons or less) such as glycol phenyl ethers (e.g.
- the second solvent is selected from the group comprising ethylene glycol 2-ethylhexyl ether, dipropylene glycol n-butyl ether, diethylene glycol n-butyl ether, propylene glycol phenyl ether, 2-pyrrolidinone, tripropylene glycol methyl ether (such as DowanolTM TPM), 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, triethyl citrate, tripropylene glycol n-propyl ether, tripropylene glycol n-butyl ether (such as DowanolTM TPnB), tetraethylene glycol dimethyl ether, and dipropylene glycol phenyl ether.
- the second solvent is selected from the group comprising ethylene glycol 2-ethylhexyl ether, dipropylene glycol n-butyl ether, diethylene glycol n-butyl ether, propylene
- the second solvent is selected from the group comprising 2-pyrrolidinone, tripropylene glycol methyl ether and tripropylene glycol n-butyl ether.
- the inkjet ink composition comprises at least about 0.1 wt% of the second solvent by total weight of the composition, for example at least about 0.5 wt%, at least about 1 wt%, at least about 1.5 wt%, or about 2 wt% by total weight of the composition.
- the inkjet ink composition comprises up to about 8 wt% of the second solvent by total weight of the composition, for example up to about 5 wt%, up to about 3 wt%, or about 2 wt% by total weight of the composition.
- the inkjet ink composition comprises the second solvent in an amount of from 0 wt% to about 8 wt% by total weight of the composition, for example about 0.1 wt% to about 8 wt% by total weight of the composition, from about 0.5 wt% to about 8 wt%, from about 0.5 wt% to about 5 wt%, or from about 0.5 wt% to about 4 wt% by total weight of the composition.
- the ink vehicle may also comprise a variety of additional components, suitable for inkjet ink compositions, selected from surfactants (for example suitable surfactants may be selected form alkyl polyethylene oxides, alkyl phenyl polyethylene oxides, polyethylene oxide block copolymers, acetylenic polyethylene oxides, polyethylene oxide (di)esters, polyethylene oxide amines, protonated polyethylene oxide amides, dimethicone copolyols, fluoroalkyl polyethylene oxides, substituted amine oxides, and the like, surfactants when present may be present in an amount from 0.01 wt% to 10 wt%), buffers, biocides (such as NuoseptTM (NudexTM Inc.), UcarcideTM (Union carbide CorpTM.), VancideTM (R.T.
- surfactants for example suitable surfactants may be selected form alkyl polyethylene oxides, alkyl phenyl polyethylene oxides, polyethylene oxide block copolymers,
- the inkjet ink composition comprises a latex polymer and an ink vehicle
- the latex polymer is derived from a composition comprising a cycloaliphatic monomer and an aromatic monomer
- the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer
- the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- the method of printing comprises curing the latex polymer, for example curing the latex polymer on the print substrate (e.g. non-porous print substrate).
- the ink vehicle comprises water and a co-solvent.
- the co-solvent for example, first solvent and second solvent (where present)
- the co-solvent should be at least partially evaporated from the ink layer such that particles of latex polymer come into close contact.
- the particles of the latex polymer may coalesce by the intermingling of polymer chains between adjacent latex polymer particles to cure the latex polymer to from a latex polymer film.
- the temperature In order for the latex polymer to be cured the temperature must be above the minimum film formation temperature (MFFT) of the latex polymer.
- Pigment particles, where present, remain in the ink layer and are embedded within the latex polymer film on curing of the latex polymer.
- the co-solvent comprises a first solvent and a second solvent.
- the first solvent is evaporated, or at least partially evaporated, before the second solvent, again due to the higher volatility of the first solvent compared to the second solvent.
- the second solvent remains in the ink layer after the water has been evaporated and the first solvent at least partially evaporated.
- the present inventors have found that the presence of a co-solvent having a boiling point of less than about 215°C (e.g.
- a first solvent) in the inkjet ink composition allows for fast drying of the inkjet ink composition to enable high throughput through a printing system.
- the present inventors have found that the presence of the second solvent in the inkjet ink composition which remain in the ink layer after evaporation of the water and at least partial evaporation of the first solvent ensure that the MFFT of the latex polymer remains lowered during the curing of the latex polymer.
- curing the latex polymer comprises evaporating water from the ink layer.
- curing the latex polymer comprises evaporating water and at least a portion of the co-solvent from the ink layer.
- Evaporation of water and at least a portion of the co-solvent allows latex polymer particles within the ink layer to coalesce into a film (“cure”). Evaporation may be facilitated in a printing system by providing heat and/or airflow. Heating may be either conductive, radiative, or convective. Airflow may comprise parallel or impinging airflow.
- heating the ink layer to evaporate water for example water and at least a portion of co-solvent comprises heating the ink layer such that the temperature of the print substrate is maintained below a temperature at which deformation (e.g. warping) of the print substrate occurs. For example, heating the ink layer such that the print substrate reaches a temperature of less than about 70 oC, for example about 65 oC or less.
- curing the latex polymer comprises evaporating substantially all of the water from the ink layer, for example evaporating at least about 95 wt%, for example at least about 99 wt%, or at least about 99.5 wt% of the water comprised in the inkjet ink composition printed as the ink layer. In some examples, curing the latex polymer comprises evaporating all of the water from the ink layer so that no water remains in the ink layer.
- curing the latex polymer comprises evaporating at least a portion of the co-solvent comprises evaporating a major amount of the co-solvent of the inkjet ink composition printed as the ink layer from the ink layer, for example evaporating at least about 80 wt%, at least about 90 wt%, at least about 95 wt%, or at least about 99 wt% of the co-solvent comprised in the inkjet ink composition printed as the ink layer.
- curing the latex polymer comprises heating the latex polymer such that latex polymer particles coalesce to form a latex polymer film.
- Forming a latex polymer film occurs after evaporation of water from the ink layer and at least partial evaporation of the first solvent and the second solvent (when present).
- Forming a latex polymer film may comprise heating the ink layer to a temperature greater that the MFFT of the latex polymer in the ink layer.
- forming a latex polymer film comprises heating the ink layer to a temperature greater that the MFFT of the latex polymer in the ink layer and a temperature less than a temperature which may cause deformation of the print substrate.
- the method of printing comprises selecting an inkjet ink composition such that the MFFT of the latex polymer is below a temperature which may cause deformation of the print substrate.
- Figure 1 is a schematic diagram of a printing system 100 comprising an inkjet printer 115 in a printing zone 110 of the printing system 100 and a drier 125 positioned in a curing zone 120 of the printing system 100.
- a print substrate may be transported through the printing system 100 along the path shown by arrow A such that the print substrate is first fed to the printing zone 110 where an inkjet ink composition is inkjet printed onto the print substrate by the inkjet printer 115 (for example from an inkjet cartridge comprising the inkjet ink composition described above) to form an ink layer on the print substrate.
- the ink layer disposed on the print substrate may then be heated in the printing zone 110 (for example the air temperature in the printing zone may range between 10oC and 90oC) such that water may be evaporated from the ink layer.
- the print substrate may then be transported to the curing zone 120 where the ink layer is heated (for example, the air temperature in the printing zone may range between 10oC and 140oC) and air is blown onto the print substrate (as shown by arrows C) such that the co-solvent is at least partially evaporated from the ink layer and the latex polymer is heated to a temperature above the MFFT of the latex polymer in the ink layer.
- the printing system 100 comprises a fan 130 for blowing air over the print substrate passing through the printing zone 110 to evaporate water from the inkjet layer.
- Printed Substrate also described herein is a printed substrate comprising a non-porous substrate on which an inkjet printed layer is disposed, the inkjet printed layer comprising a latex polymer, wherein the latex polymer comprises cycloaliphatic monomer and an aromatic monomer, wherein the cycloaliphatic monomer comprises a cycloaliphatic (meth)acrylate monomer or a cycloaliphatic (meth)acrylamide monomer and the aromatic monomer comprises an aromatic (meth)acrylate monomer or an aromatic (meth)acrylamide monomer.
- Low energy surface media include polyolefinic media (polypropylene or polyethylene). These media may be factory modified to facilitate wetting by inks (e.g. aqueous inkjet inks); generally, this modification increases the surface energy, but relative to other substrates they remain 'low'. Surface energy, for example surface energy with respect to aqueous inks, may be measured by contact angle between the substrate and water.
- a low energy surface media is a media (i.e. print substrate) having a surface energy of less than about 40 dyne/cm, for example less than about 35 dyne/cm. The surface energy of a print substrate may be measured accroding to ASTM D2578.
- Example 1– latex 1 [000129] A latex polymer was prepared as follows. Water (138g) was heated to 77°C with mechanical agitation. At 77°C, latex seed (4.4g; 67nm particle size) was added to the reactor. At 77°C, potassium persulfate (0.36g) dissolved in water (4% solution) is added.
- an aqueous emulsion comprised of water (39.4g), copolymerizable surfactant (Hitenol ® AR-10) (4.9g), cyclohexyl methacrylate (124.6g), cyclohexyl acrylate (18.0g), phenoxyethyl methacrylate (25.2g) and methacrylic acid (7.2g); and a 4% aqueous solution (18.3g) of potassium persulfate.
- Residual monomer was reduced using high temperature 85°C followed by (7.5g) 5% solution of ascorbic acid and 5% solution of (15.2g) tert-butyl hydroperoxide at 70°C.
- aqueous emulsion comprised of water (28.2g), copolymerizable surfactant selected from Hitenol ® BC-10, BC-30, KH-05 or KH-10 (1.5g), methyl methacrylate (91.1g), styrene (24.1g), butyl acrylate (4.8g), and methacrylic acid (0.6g).
- Residual monomer was reduced as described in Example 1. After cooling to near ambient temperature, pH is adjusted to 8 with dilute potassium hydroxide; inkjet suitable aqueous biocides are added.
- the resulting acrylic latex is 41% solids by total weight of latex emulsion; particle size 0.22 ⁇ m; viscosity less than 50 cp.
- Comparative Example 3– latex 3 [000133] Water (138g) is heated to 77°C with mechanical agitation. At 77°C, latex seed (4.4g; 67nm particle size) is added to the reactor. At 77°C, potassium persulfate (0.36g) dissolved in water (4% solution) is added.
- an aqueous emulsion comprised of water (39.4g), copolymerizable surfactant selected from Hitenol ® AR-10, BC-10, BC-30 (4.9g), cyclohexyl methacrylate (124.6g), cyclohexyl acrylate (18.0g), styrene (25.2g) and methacrylic acid (7.2g); and a 4% aqueous solution (18.3g) of potassium persulfate.
- Residual monomer was reduced as described in Example 1. After cooling the near ambient temperature, pH is adjusted to ⁇ 8 with dilute potassium hydroxide; inkjet suitable aqueous biocides are added.
- the resulting acrylic latex is 41% solids by total weight of latex emulsion; particle size 0.22 ⁇ m; viscosity less than 50 cp.
- a black inkjet ink composition was then produced using each of the latex polymers produced in Example 1 and Comparative Examples 2 and 3. The formulation of each of the black inkjet ink compositions produced is set out in Table 1 below. [000136] Table 1:
- Inks 1-3 were tested by inkjet printing each of the inks using a latex inkjet printer directly (i.e. with no primer or pre-treatment applied before printing of the inks) onto non-porous and rigid substrates, a polypropylene substrate and a vinyl substrate.
- the inks were cured at 70°C following printing on to the polypropylene substrate and at 110°C following printing on to the vinyl substrate.
- a lower curing temperature was used following printing on the polypropylene substrate as higher temperatures were found to cause warping of the polypropylene substrate, whereas the vinyl substrate is able to withstand the higher curing temperature.
- Samples of each of the printed substrates were subjected to the following three tests.
- Windex Blue ® window cleaner rub resistance was measured using a Taber ® linear abraser model 5750 equipped with an acrylic crockmeter tip covered with polyester cloth. The cloth was dipped in the rubbing fluid, and the printed image was rubbed 5X with 600g pressure. Plot damage and wiper cleanliness are graded with the following scale:
- 70% 2-Propanol Rub Resistance Test [000141] 70% IPA rub resistance was measured using a Taber ® linear abraser model 5750 equipped with an acrylic crockmeter tip covered with polyester cloth. The cloth was dipped in the rubbing fluid, and the printed image was rubbed 5X with 600g pressure. Plot damage and wiper cleanliness are graded with the following scale:
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2017/015902 WO2018143959A1 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
EP17894844.4A EP3494150B1 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
KR1020197011813A KR102182193B1 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
US16/329,990 US11142604B2 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
CN201780068117.5A CN109983042B (en) | 2017-01-31 | 2017-01-31 | Latex polymers |
BR112019008917-9A BR112019008917B1 (en) | 2017-01-31 | 2017-01-31 | Latex polymers, ink composition and inkjet printing method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2017/015902 WO2018143959A1 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2018143959A1 true WO2018143959A1 (en) | 2018-08-09 |
Family
ID=63040980
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2017/015902 WO2018143959A1 (en) | 2017-01-31 | 2017-01-31 | Latex polymer |
Country Status (6)
Country | Link |
---|---|
US (1) | US11142604B2 (en) |
EP (1) | EP3494150B1 (en) |
KR (1) | KR102182193B1 (en) |
CN (1) | CN109983042B (en) |
BR (1) | BR112019008917B1 (en) |
WO (1) | WO2018143959A1 (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102019105912A1 (en) * | 2019-03-08 | 2020-09-10 | Canon Production Printing Holding B.V. | Method and drying unit for drying a liquid mixture |
US11608403B2 (en) | 2020-11-24 | 2023-03-21 | Xerox Corporation | High viscosity latexes |
US11643540B2 (en) | 2021-05-25 | 2023-05-09 | Xerox Corporation | Seeded emulsion polymerization process for latexes and aqueous inkjet ink compositions made therefrom |
US11708504B2 (en) | 2020-11-24 | 2023-07-25 | Xerox Corporation | Aqueous inkjet ink compositions made from monodisperse latexes |
US11714361B2 (en) | 2021-07-27 | 2023-08-01 | Xerox Corporation | Toner |
US11781025B2 (en) | 2021-05-06 | 2023-10-10 | Xerox Corporation | Aqueous inkjet ink compositions |
US11834580B2 (en) | 2021-07-27 | 2023-12-05 | Xerox Corporation | Ink composition with pH responsive resin particles |
US11919982B2 (en) | 2021-12-09 | 2024-03-05 | Xerox Corporation | Latexes with phosphoric acid functional resin particles |
US11952448B2 (en) | 2021-07-27 | 2024-04-09 | Xerox Corporation | Organic additives and compositions containing the same |
US11952451B2 (en) | 2021-07-27 | 2024-04-09 | Xerox Corporation | Latexes with pH responsive resin particles |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113136264A (en) * | 2021-04-25 | 2021-07-20 | 广东富行洗涤剂科技有限公司 | Glue removing liquid and process for removing curing glue in optical prism glass processing |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999023182A1 (en) * | 1997-10-31 | 1999-05-14 | Hewlett-Packard Company | Latex polymer blends for ink-jet inks |
US20050007432A1 (en) * | 2002-09-24 | 2005-01-13 | Miharu Kanaya | Ink composition for ink-jet recording, recording method using same, and record |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5736692A (en) * | 1980-08-14 | 1982-02-27 | Fuji Photo Film Co Ltd | Sheet for ink jet recording |
DE3902557A1 (en) * | 1989-01-28 | 1990-08-02 | Roehm Gmbh | AQUEOUS POLYACRYLATE SYSTEM FOR THE FINAL PAINTING OF POLYVINYL CHLORIDE SURFACES |
DE3902555A1 (en) * | 1989-01-28 | 1990-08-02 | Roehm Gmbh | WAFERRED POLYACRYLATE SYSTEMS FOR PAINTING PLASTIC SURFACES |
US7040747B2 (en) * | 1999-07-30 | 2006-05-09 | Seiko Epson Corporation | Recording method for printing using two liquids on recording medium |
US6184268B1 (en) | 1999-08-30 | 2001-02-06 | Xerox Corporation | Ink jet ink compositions and processes thereof |
JP2003238888A (en) | 2002-02-13 | 2003-08-27 | Mitsubishi Rayon Co Ltd | Coating resin composition and its preparation process |
US7411011B2 (en) | 2003-03-31 | 2008-08-12 | Hewlett-Packard Development Company, L.P. | Latex-based overcoat for ink-jet printing applications |
US7696262B2 (en) | 2003-12-19 | 2010-04-13 | Hewlett-Packard Development Company, L.P. | Wetting agent combinations for inkjet printing |
US8440742B2 (en) | 2004-02-05 | 2013-05-14 | Hewlett-Packard Development Company, L.P. | Polymer colloid-containing ink-jet inks for printing on non-porous substrates |
US10072168B2 (en) | 2005-10-13 | 2018-09-11 | Hewlett-Packard Development Company L.P. | Marking fluids for vinyl substrates |
WO2007097049A1 (en) | 2006-02-24 | 2007-08-30 | Teikoku Printing Inks Mfg. Co., Ltd. | Process for producing ink and relevant to the process, ink, printed matter and molding |
US7744205B2 (en) | 2006-03-17 | 2010-06-29 | Hewlett-Packard Development Company, L.P. | Solvent/latex binder system for heated inkjet printing |
US8114923B2 (en) | 2006-03-27 | 2012-02-14 | Hewlett-Packard Development Company, L.P. | Inkjet ink solvent system |
WO2009011692A1 (en) | 2007-07-13 | 2009-01-22 | Hewlett-Packard Development Company, L.P. | Ink-jet compatible latexes |
US8267505B2 (en) | 2007-12-14 | 2012-09-18 | Hewlett-Packard Development Company, L.P. | Inkjet inkset and methods |
KR20100099287A (en) | 2007-12-14 | 2010-09-10 | 휴렛-팩커드 디벨롭먼트 컴퍼니, 엘.피. | Improved color and durability of ink-jet ink sets with added latex |
KR20100020172A (en) | 2008-08-12 | 2010-02-22 | 동우 화인켐 주식회사 | Printing ink composition for color filter, color filter, and liquid crystal display device having the same |
JP5467744B2 (en) * | 2008-09-02 | 2014-04-09 | 富士フイルム株式会社 | Ink set for ink jet recording and image recording method |
JP5581815B2 (en) | 2009-06-05 | 2014-09-03 | 東洋インキScホールディングス株式会社 | Binder resin composition for aqueous inkjet ink and inkjet ink using the same |
EP2449039B1 (en) | 2009-06-30 | 2017-03-15 | Hewlett-Packard Development Company, L.P. | Ink-jet overcoats including latex polymers and inorganic nano particles |
JP5518397B2 (en) * | 2009-08-12 | 2014-06-11 | 富士フイルム株式会社 | Aqueous ink composition, composite particle manufacturing method, ink set, and image forming method |
US8851649B2 (en) | 2011-05-13 | 2014-10-07 | Eckart Gmbh | UV ink jet printing ink composition |
JP5996894B2 (en) | 2012-03-13 | 2016-09-21 | 株式会社タムラ製作所 | Transparent resin composition for insulating film formation |
WO2014042651A1 (en) | 2012-09-14 | 2014-03-20 | Hewlett-Packard Development Company, L.P. | Latexes and associated ink-jet inks |
IN2015DN01911A (en) | 2012-09-14 | 2015-08-07 | Hewlett Packard Development Co | |
US8783842B2 (en) | 2012-09-14 | 2014-07-22 | Hewlett-Packard Development Company, L.P. | Methods and systems for printing on non-porous media |
CN104662108B (en) | 2012-09-25 | 2017-05-17 | 惠普发展公司,有限责任合伙企业 | Fluid sets for printing |
US20140128541A1 (en) * | 2012-11-06 | 2014-05-08 | Xerox Corporation | Latex process to enable high loadings of hydrophobic monomers |
US9279059B2 (en) | 2013-01-22 | 2016-03-08 | Xerox Corporation | Latex ink containing a latex having a bimodal molecular weight distribution for indirect printing method |
BR112017013475B1 (en) * | 2014-12-24 | 2023-02-07 | Swimc Llc | METHOD FOR FORMING A COATING OVER A FOOD OR BEVERAGE CONTAINER, ARTICLE, AND, INTERNAL SPRAY COATING COMPOSITION. |
-
2017
- 2017-01-31 US US16/329,990 patent/US11142604B2/en active Active
- 2017-01-31 WO PCT/US2017/015902 patent/WO2018143959A1/en unknown
- 2017-01-31 CN CN201780068117.5A patent/CN109983042B/en active Active
- 2017-01-31 EP EP17894844.4A patent/EP3494150B1/en active Active
- 2017-01-31 BR BR112019008917-9A patent/BR112019008917B1/en not_active IP Right Cessation
- 2017-01-31 KR KR1020197011813A patent/KR102182193B1/en active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999023182A1 (en) * | 1997-10-31 | 1999-05-14 | Hewlett-Packard Company | Latex polymer blends for ink-jet inks |
US20050007432A1 (en) * | 2002-09-24 | 2005-01-13 | Miharu Kanaya | Ink composition for ink-jet recording, recording method using same, and record |
Non-Patent Citations (1)
Title |
---|
See also references of EP3494150A4 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102019105912A1 (en) * | 2019-03-08 | 2020-09-10 | Canon Production Printing Holding B.V. | Method and drying unit for drying a liquid mixture |
DE102019105912B4 (en) * | 2019-03-08 | 2020-10-01 | Canon Production Printing Holding B.V. | Method and drying unit for drying a liquid mixture |
US11427024B2 (en) | 2019-03-08 | 2022-08-30 | Canon Production Printing Holding B.V. | Method and dryer system for drying a fluid mixture |
US11608403B2 (en) | 2020-11-24 | 2023-03-21 | Xerox Corporation | High viscosity latexes |
US11708504B2 (en) | 2020-11-24 | 2023-07-25 | Xerox Corporation | Aqueous inkjet ink compositions made from monodisperse latexes |
US11781025B2 (en) | 2021-05-06 | 2023-10-10 | Xerox Corporation | Aqueous inkjet ink compositions |
US11643540B2 (en) | 2021-05-25 | 2023-05-09 | Xerox Corporation | Seeded emulsion polymerization process for latexes and aqueous inkjet ink compositions made therefrom |
US11714361B2 (en) | 2021-07-27 | 2023-08-01 | Xerox Corporation | Toner |
US11834580B2 (en) | 2021-07-27 | 2023-12-05 | Xerox Corporation | Ink composition with pH responsive resin particles |
US11952448B2 (en) | 2021-07-27 | 2024-04-09 | Xerox Corporation | Organic additives and compositions containing the same |
US11952451B2 (en) | 2021-07-27 | 2024-04-09 | Xerox Corporation | Latexes with pH responsive resin particles |
US11919982B2 (en) | 2021-12-09 | 2024-03-05 | Xerox Corporation | Latexes with phosphoric acid functional resin particles |
Also Published As
Publication number | Publication date |
---|---|
CN109983042A (en) | 2019-07-05 |
EP3494150A4 (en) | 2019-09-04 |
EP3494150B1 (en) | 2021-07-07 |
US20190194372A1 (en) | 2019-06-27 |
KR20190058573A (en) | 2019-05-29 |
KR102182193B1 (en) | 2020-11-24 |
BR112019008917A2 (en) | 2019-07-16 |
US11142604B2 (en) | 2021-10-12 |
BR112019008917B1 (en) | 2022-06-21 |
EP3494150A1 (en) | 2019-06-12 |
CN109983042B (en) | 2021-10-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11142604B2 (en) | Latex polymer | |
US10876012B2 (en) | Inkjet printing system | |
EP3494183B1 (en) | Inkjet ink composition and inkjet cartridge | |
EP0633914B1 (en) | An aqueous ink composition | |
US10829659B2 (en) | Method of inkjet printing and fixing composition | |
US20060007287A1 (en) | Wetting agent combinations for inkjet printing | |
EP2358830B1 (en) | Pigmented ink-jet inks with gloss-enhancing polymers | |
US20230095396A1 (en) | Method of printing | |
US11401408B2 (en) | Polymer particles | |
US10072166B2 (en) | Inks with latex polymers having improved printing performance | |
US20230104817A1 (en) | Over-print varnish formulation | |
WO2023091136A1 (en) | Multi-phase latex particle composition | |
WO2023091135A1 (en) | Inkjet fluid set |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 17894844 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2017894844 Country of ref document: EP Effective date: 20190306 |
|
ENP | Entry into the national phase |
Ref document number: 20197011813 Country of ref document: KR Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112019008917 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112019008917 Country of ref document: BR Kind code of ref document: A2 Effective date: 20190502 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |